Preparing a Boy For His Sister

By NAMB

modestnot@gmail.com

Copyright 2023 by NAMB all rights reserved

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This story is intended for adults only. It contains depictions of forced nudity, spanking, and/or sexual activity of preteen and young teen children. This is fantasy, and the author in no way endorses or practices these things on real life. If you are not of legal age in your community to read or view such material, please leave now. 
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Prepared for Sister

A babysitter conditions a girl’s older brother to accept female domination in exchange for sexual pleasure. This story was inspired by the picture by the artist Roadkill (AKA Rotex) of an older girl fondling the penis of a completely naked boy about the age of the one in this story.

-=o=-

The status was quo at the Barnes house for nearly a decade. Mrs. Price the widower next door had taken care of the Barnes children since Robert was a three-year-old toddler and his sister Amelia was still a one-year-old in diapers.

The Barnes enjoyed having her as their babysitter. She was good with children even though she never had any of her own. Nonetheless, she enjoyed playing with them and had the spirit to discipline them in just the right measure when needed. Children responded to her with both respect and love. It was a mutually satisfying relationship: she liked kids, the kids like her and the parents could not say enough nice things about her.

It was with great sadness that the Barnes had to see her go. Her mother’s health was failing, and Mrs. Price decided to move across the country and be with her to be her caregiver. She had been a part of the family on almost every Saturday night for more than 10 years. She was there for every major milestone in the children’s lives.

It was also with great concern that the family looked for her replacement. It’s difficult to find a 40-year-old woman, as Mrs. Price was when she started, who was interested in a babysitting job. It soon became obvious that they would have to “settle” for a college or even high school student.

They asked everybody they knew for recommendations and found that all the “good” sitters were already employed. Except for one: Chole Kelley. Chole was the babysitter for the Everetts. She came on board after Mrs. Everett and Mr. Everett separated. Once their divorce was settled, Mrs. Everett and her children moved out of state leaving Chole without a job.

The Barnes put Chole and a half dozen other girls through a grueling interview process: interrogation would be closer to the truth. Even though she was only 15, Chole proved to be far superior to the rest of the candidates all of whom were older than her. It was about the only thing she had in her favor – on paper: the prospect of longevity. She would probably stay on the job longer than a 19-year-old.

What sold her was her experience; she had been babysitting since she was 12, her cheerful disposition and the way she held herself with confidence. The Barnes were also impressed with her views on discipline: fair, consistent and carefully weighing the punishment against the crime. It was obvious that she would not be abusive, but she would keep the children within safe boundaries.

-=o=-

Robert was upset with his parent’s decision. “Mom, I don’t need a babysitter. I’m 13 years old. I can take care of myself.”

“I’m not so sure of that. There’s also the matter of looking after Amelia.”

“She’s 11. She’s a big girl. She can take care of herself, too.”

“No she can’t. I can trust the both of you for a short while during the day like when I go shopping. You dad and I are going to be out for most of the evening. I like the idea of having an older person in the house for the purposes of safety.”

“Mom, I’m 13 years old. There are kids in my class who are already babysitting other people’s kids. They’re all girls, but still, if they are old enough to babysit, then I should be old enough.”

“That’s not the point. Things are different with girls; they’re more responsible.”

“You’re being sexist. That’s not fair.”

“I’m not being sexist. It’s a proven scientific fact: girls mature faster than boys in almost every way. Chole is 15 and she is responsible enough.”

“15? That’s barely older than me. You’re telling me I’m going to have to listen to a girl?”

“Yes, I am. If you behave yourself, you won’t have to listen to her. She’s not here to boss you around; she here to see that you and Amelia stay safe.

She’s your babysitter whether you like it or not. If you so much as give her a hard time, you’ll have to deal with your father. Who knows, you may even turn out to like her. Give her a chance.”

Robert muttered an obscenity under his breath, but managed to grumble out, “OK, mom.”

-=o=-

Robert was surprised when he saw Chloe. There were women on the internet that didn’t look as good as she did. Even Leah Sullivan, the hottest girl in his class by unanimous vote of all the boys as they raised their penis in honor of her as if to say “aye,” didn’t come close.

Chole went in and out in all the right places. Her body was more athletic than voluptuous, but that was a shape that intrigued young Robert.

He found himself getting hard just looking at her. That never happened with old Mrs. Price. He wondered how he would fare once Chole invaded his fantasies as he was sure she would.

His mother made the introductions, “Robert, Amelia, I would like you to meet Chole, that’s Ms. Chole to you. She will be your new babysitter.

Chole, this is Robert. He’s 13 and will be going into 7th grade his fall.”

Robert blushed as she looked at him and she smiled back at him. He knew she could see the bulge in his pants. The girls in his class teased the boys every time they spotted one with a hard on. If his classmates knew what was going on “under the hood” with boys, he was certain that Chole, who undoubtedly had more experience with boys, knew exactly the effect she was having on his body.

Robert was so smitten with Chole, he didn’t even hear his mother introducing her to his sister.

Once the parents left, Chole had the two children sit with her in the living room. “I’d like to take some time to get to know the two of you better and get you to know me better. I’m sure that we’ll get to know each other better as time goes on and we won’t have to be so formal.

We’ll start with me. My name is Chole. I am named after my grandmother. I’m 15 and going into my Sophomore year at Renton High. I play tennis and soccer and I like to swim. I have an older sister who is in college and I’ve been babysitting for about 3 years.

You were there when your mom went over the house rules with me. These are her rules and I expect you to obey them. If you do obey them, we’ll get along just fine. If you don’t obey then you will face consequences you won’t like. Your parents gave me a lot of leeway in administering discipline."

“You’re not going to spank us?” Amelia interrupted.

“That’s one of the options, but I usually like to find more creative ways to modify behavior.”

Chole went on the question the two children about school, what sports they played, who their friends were and general information.

Of the two, Amelia was the more enthusiastic, opening up almost immediately and even volunteering information. Robert was more terse in his responses, but eventually opened up as well.

As well as being an erection-provoking goddess, she was also warm and friendly. The girls in his class were so stand-offish.

Chole finished her conversation with the kids with, “I’m going to bake up a batch of chocolate-chip cookies. Who would like to help me?’

Amelia’s hand shot up like she was sitting at her desk at school.

“What about you, Robert?”

“Baking cookies is for girls. I’m going up to my room to play some games.”

“OK. We’ll call you when the cookies are ready.”

Amelia and Chole got busy in the kitchen.

Chole said, “It’s a good thing your brother went upstairs. This gives us some opportunity for some ‘Girl Talk.’ Tell me some interesting things about your brother.

“Rob’s not too bad for a boy. Most boys in my class are just, well, kind of jerks. They are almost like babies. I wish they would grow up.

Even Rob is kind of like that. He’s a bit better than the boys in my class. Yet, he’s two years older than me and so childish. He’s constantly picking on me. Somehow, he thinks that makes him superior to me.

We used to get along a lot better when we were kids, but in the last year or two, he thinks he’s Mr. ‘I’m so important because I’m a boy.’

My friends think he’s cute, but they don’t have to live with him.

On the other hand, he does try to look out for me. He is capable of doing nice things for me when he feels like it.”

“Don’t take it to badly, Amelia, Rob’s just going through a phase most boys his age are going through. They’re not little boys anymore and they want to prove how independent and macho they are.

Doing things like getting hugs from mom or an aunt or being nice to kid sisters embarrasses them.

He’s just overreacting. How can he be a big man with his friends when he’s nice to little girls?

Right now, he’s more out to impress his peers than he is to impress girls. That will change when he gets older and more mature.

What most boys never seem to get is how much girls judge boys by how they treat other girls, not just the ones that interest them.”

The two girls had a pleasant conversation as the aroma of baking cookies filled the kitchen. The oven “dinged” and Chole removed the sheet and placed it on top of the stove.

“We’ll let them cool for about 10 or 15 minutes. Let’ go up and see how your brother is doing.”

As they approached Rob’s room, Amelia said, “His door is closed. He’s not supposed to do that. Mom and dad made that rule a couple of months ago. I don’t know why.

I’m allowed to close my door for privacy.”

“Shh. Let’s see if we can surprise your brother.”

“Yeah, maybe if we rush in and make a loud noise, we can scare him.”

As the girls gathered outside his door, they could hear some grunting sounds.

“I wonder what kind of game he could be playing that makes that noise?”

Chloe knew that sound. She had heard it before. She knew what boys did to produce it.

She grabbed the girl aside and whispered to her, “I think you’re in for a surprise. What you may see might shock you. You’ll be OK. I’m with you. I’ll take care of everything. Trust me.”

“What am I going to see?”

“Do you know what boys look like?”

“Of course, I do. My friend, Sarah, has a baby brother. I help her change his diapers all the time.”

“I mean bigger boys.”

“Sarah and a girl named Emily and me made Ryan Stewart make pee for us. We were all in the first grade at the time.

Why are you asking me these questions?”

“Because what we might see is your brother naked. Have you ever seen him naked?”

“I kind of remember taking a bath with him as a little girl. I really don’t remember that much about it.”

“Don’t worry, you’ll be OK. Just follow my lead and everything will be OK.”

The girl nodded in response.

Both girls put their hands up to the door. Chloe mouthed a, “One, two, three” and the two girls pushed the door open. With their combined force, it swung back with a bang as it slammed open against the wall.

That was enough to startle the poor boy who was at his desk looking at the monitor on his computer with his back to the door.

If that weren’t enough, the two girls came in yelling. Chloe was screaming and Amelia was screeching that high pitched sound that only pre-teen girls are capable of producing.

What the girl saw both shocked and disgusted her. Her brother, as Chloe had predicted was at least partially naked: his pants were pulled down below his knees and he seemed to have his hands in his lap.

Her brother’s semi-naked appearance was not the main cause of her reaction; she could see little of him.

It was what was on the screen that caused her stomach to solidify. It was a movie of a woman and she was licking the head of a man’s penis.

Rob frantically started clicking the mouse to close the browser and stop the video. It was too late. Both females had already seen enough. He knew that he was in trouble enough just for that and then he still had the issue of his partial nudity to explain.

Chloe laughed when he stood up. He was trying to both hide his private parts and pull up his pants at the same time and having absolutely no success with the latter and hardly any with the former.

“Stop! Stand still!” Chloe commanded.

The boy obeyed and started crying, “Please don’t tell my parents. They’ll take away my computer this time.”

“So you’ve done this before.”

He nodded his head.

“I won’t tell your parents. We can talk about this sensibly.”

“What about her,” Rob said, indicating his sister with a movement of his head.

“Amelia has seen enough. She’s part of this now, so she will be part of the agreement.

I think we can come to a solution that will satisfy everyone.

The first thing I want you to do is to get completely naked. Everything off, even socks.”

“I can’t do that, you’ll see me.”

“There is nothing wrong with that. I’ve seen boys before and so has your sister. You don’t have anything that we girls have not seen before.

It’s a non-negotiable part of the deal. If you don’t do it then both of us will tell your parents.”

“Should I leave?” Amelia asked.

“No, stay. You’re a part of the plan and I think you’ll like your role in it. Besides there is a tremendous learning opportunity here.”

Turning to the boy Chloe said, “Get stripping.”

He got naked but was facing away from the girls.

“Turn around. Hands at your sides and face your sister and me.”

Rob felt totally humiliated. Here was the girl that promised to be the star of his fantasies and she was looking at his naked body. His sister, who he though of as “just a little girl,” was also present and witness to his shaming.

“Now tell us what you were doing.”

“N-nothing.”

“You definitely were doing something, and I know what it was. Now tell your sister.”

“I was jerking off.”

“That’s better.”

“What’s jerking off,” Amelia asked.

“It’s a type of masturbation. We can talk about it later, “ the babysitter replied, “Why were you jerking off?”

“I felt. I don’t know. I just felt like doing it.”

“Your penis is sticking straight out. I think that’s the answer.”

“What?” the boy and his sister responded in stereo.

Chloe explained, “When a boy gets sexually excited, his penis gets hard and it gets bigger like your brother’s is now.

From what I’ve heard, it’s not painful, but it does put a boy on edge. It’s an uneasy feeling.

One way to make it go away is masturbation: rub the penis until it ejaculates.”

Turning back to Rob, Chloe asked, “Does it feel good when you cum?”

Rob nodded.

“That’s the real reason you do it, isn’t it? It feels good.”

“I never thought about it that way.”

“Come here.”

The boy stood before her. She got down on her knees in front of him. She took one hand and wrapped it around his waist and drew him closer to her. She gently palmed his erected penis in her other hand.

“There is nothing to be ashamed of. Your feelings are perfectly normal. All boys have them.”

He lowered his head and closed his eyes.

“Raise your head and look at me. I want your eyes on mine.”

Blushing profusely, he obeyed.

“As I said, there is nothing to be ashamed of. Every boy does what you were just doing. But we’re going to make you an offer every boy does not get.

There’s a reason you had your door closed. You were ashamed of what you were doing. Now your sister and I know what you were doing, you don’t have to hide it from either of us anymore.

There is a reason I made you get totally naked. I want you to get comfortable being naked in front of us. You have nothing to hide from us. From now on, whenever your parents are out, you will be naked. You will eventually become comfortable with your own body and stop being ashamed of it.

Think about it. No more hiding in your room. No more waiting until you can ditch your sister to do it. You can do it in front of her with no shame. You can even enjoy her doing it to you. I know a couple of ‘tricks’ I could teach her that will make you feel like you’ve never felt before.

We will keep it just between ourselves. There is no reason for your parents to find out. Do you agree?”

“Yes.”

“There is a price to pay. You will have to stop picking on your sister and be nice to her.”

“OK.”

“And you will have to do it when she tells you.”

“OK”

“And you can’t do it unless she tells you, so no jerking off on your own without her permission.”

This demand earned a frown, but also got an OK.

“Good. Now show us what you were doing. We’ll sit here on the bed and watch you do it. Make sure you look at us while you are doing it. Looking at a girl while jerking off in front of her is telling her that your are doing it for her enjoyment and not yours.

When you get done, we’ll let you rest and then let Amelia have a hand at trying it on you.”

The boy went on to perform the act for his female audience. Chloe, having witnessed the act before with other boys, provided commentary and prompted Amelia to pay attention as he approached climax.

Chloe challenged Amelia to experiment with her brother’s cum, taking it on her fingers and rolling it between them, then sniffing it and finally taking a drop and tasting it.

The girls left Rob, laying on his bed to recover.

“Clean your mess up,” Chloe commanded. “Then come down and have some cookies. And stay naked. Your sister still needs her chance with you.”

As the girls returned to the kitchen, Amelia asked, “You said that we had to keep this just between us. Sarah and Emily are my BFFs. I can’t keep this a secret from them.”

“There will be time for that. Give it a couple of weeks. First we have to make sure we can trust them. Give me a chance to talk to them.”

Amelia hugged her and gave her a kiss.

Later that evening, after Amelia masturbated her brother and after he cleaned it up and after he got dressed and after his parents came back and after Chole departed, Rob and his sister had a chat about the events of the evening.

“I was so scared when you guys walked in on me.”

“To tell you the truth, so was I. Chloe sure handled the situation though, didn’t she?”

“Yeah. I was glad she didn’t tell mom and dad. I was concerned about what kind of punishment she would come up with. If this is punishment maybe I should misbehave more often.”

“Then you like the idea of me being in charge of your masturbation?”

“Why not? You like seeing it and doing it. I get to feel good without feeling guilty and we can do it almost all of the time.”

“So you wouldn’t mind if I invited Sarah and Emily to watch?”

“Why not? They’re kind of cute. I think I’d have fun doing it for them, too.”










(End of File)